East Coast Prep with a Twist feat. F.E. Castleberry

December 5th, 2011

I have to admit, I don’t read many other blogs. Once I’m finished with everything it takes to manage and expand TheStyleBlogger, it’s usually time to shut my computer.

Ever since Jenilee introduced me to Unabashedly Prep, however, I’ve enjoyed watching F.E. Castleberry carve a niche by documenting the East Coast Prep subculture while strategically bending, but not breaking, it’s strongly rooted traditions.

As a fashion photographer turned style blogger, F.E. has an equally great eye behind the camera as he does for putting together outfits that are in-line with the traditional prep aesthetic but carefully updated for a modern appeal.

Here, Fred gives us a taste of some of the layered looks he’s wearing this Fall.

    1. Tailored Sportswear

    “While a down vest is easily  imagined over a flannel shirt or a Norwegian sweater, I began wearing mine over my sport coats after seeing some Italian do it last year. My style is heavily rooted in American sportswear, thus the tailored clothing/sportswear contrast feels good to me.”

    “My vintage Omega Seamaster wristwatch is my favorite piece in my wardrobe.  I wear it everyday. In the spring/summer I pair it with colorful striped nylon bands while in the fall/winter I keep it grounded with a dark brown alligator strap.”

    • Navy down vest by Penfield
    • Khaki chinos by Club Monaco
    • Brown leather wingtips by Vintage Cole Hann
    • Tortoise eyeglasses by Lookmatic
    • Navy/yellow striped socks by Norman Hilton
    • Red/green striped tie by Brooks Brothers
    • Pink stripe oxford shirt by Taylor Stitch
    • Watch Vintage Omega Seamaster

    2. Do it Yourself

    “These chinos could be considered controversial.  They are a nod to my artistic youth and Jackson Pollack during his years in the Hamptons. He splattered huge canvases laid out on the floor of this barn. You either get them or you don’t.  While you can’t wear them too often, I know I’m the only guy doing so when I do.”

    “I like to play with textures, patterns, and fabrics.  Here, that attitude is personified with denim, cotton, tweed, silk, tartan, and sterling silver.”

    3. Old World Casual

    “Even when I’m casual, I’m not too casual.  I have a tendency to mix casual wear with suiting/sportcoats and dress with a wink and a smile.  This look is a variation on my sport coat/jeans uniform. The wool tartan belt hits its stride when it’s not competing with any other pattern.”

    “While I don’t wear slippers outside too often, when I do around the holidays, my monogrammed slippers start more conversations than I seem to anticipate. Great ice breaker at holiday mixers.”

    • Navy polka dot pocket square
    • Grey cable knit crewneck sweater by Ralph Lauren
    • Tan corduroy jacket by Rugby
    • Tartan plaid wool d-ring belt by Ralph Lauren
    • Tortoise eyeglasses by Lookmatic
    • Light blue oxford shirt by Rugby
    • Raw selvedge denim by Rugby
    • Navy monogrammed slippers by Del Toro

    4. Straight East Coastin’

    “Ribbon belt (and orange at that) with a suit? It just reiterates I don’t take myself too seriously even in dark navy/gray tones. And yes”¦if the leaves are still in the trees, my ankles are still feeling the breeze.”

    • Grey flannel suit by Rugby
    • Navy trench coat by Club Monaco
    • Blue bengal stripe shirt by Ascot Chang
    • Navy polka dot silk knit tie by Brooks Brothers
    • Brown double monk strap shoes by Ralph Lauren
    • Orange stripe ribbon belt by Ralph Lauren
    • Navy waxed cotton weekend duffle by Ernest Alexander
    • Tortoise eyeglasses by Lookmatic

    Thanks, as always, for reading – and special thanks to F.E. for participating.

    Yours in style,

    Dan Trepanier


    Photography by Michael Norwood. 

    • TTG

      Great post! I love all four looks, especially how good the readers look on him and the monogrammed slippers. Was never too sure about the slippers but i think i might give it a try after all. Will also be checking out F.E.’s blog.


    • jack

      Good stuff.

      Looks are impressive. Very stylish man.

      This guy, like you Dan knows how to dress.

    • Hailie Durrett

      Oh, this post only further verifies my blogger crush on FEC. What a stud! Keep up the good work.

    • HarrisonK


      It seems like you wear a sport coat and tie quite frequently, however, I’ve been noticing that you tend to wear OCBD (or other type of “sport shit”) with the sport coat and tie, rather then dress shirts. Is there any reason you don’t wear dress shirts when wearing a sport coat and tie?

    • I.D. Patterson

      Love look 3, beautifully summed up in the second picture. The contrast in texture between the corduroy blazer and cable-knit sweater is glorious.

      All the best.

    • Alex B

      Look #1 and #3 are really fun. Enjoy both of your blogs.

      Thumbs up!

    • Carter

      You’re killing it in this post! The ribbon belt is so sick. Saw a pic of you on another blog wearing a red blazer w/ dark denim…need that blazer! Keep it up.
      Be Well

    • BVW

      Looks 1 and 3 are sharp. And it’s Jackson Pollock

    • A.K MOREY

      I follow FEC’s blog regularly and agree that he has good style, however, some of his ensembles come close to costume territory. To illustrate the point, think of the painted chinos which clearly lack authenticity as I highly doubt J.P suddenly decided to splash paint all over his pants one day like FEC. Intentionally distressing clothing is both a waste time and money in a sense that you’ll never get the same utility out of the painted pants and you just put oil paint on $200 chinos. Part of the beauty in owning a patina/ distressed object is watching it evolve and change from pristine to better with age.

      PS. I also must add that I agree with JAileen, maybe some can pull off the look (6’2 155 lb models) but us regular dudes end up looking mighty stout.

      • F.E. Castleberry


        Let’s breathe together on the count of 3…1, 2, 3 [BEATHE]…you may take yourself very seriously but please don’t assume I do.

        I have fun in life, especially when it comes to dressing myself. These pants are *inspired* by my artistic youth and Jackson Pollack’s time spent in his barn studio in the Hamptons. I never proclaimed they were exact replicas—just inspired by. That’s what aspirational designers do that make the very clothes most of us walk around in.

    • paul frederick

      Thats cool i like it. Good post. Always gives me new ideas

      • F.E. Castleberry


        That’s what it is all about…new ideas. All the best.

    • NY

      Ah, preppy style. I love the passion you guys both bring to the table, but as an old timer I find this all rather comical. Every new generation claims to be “reinventing” fashion, or “improving” upon it, or “reinvigorating” it. The fact of the matter is DT and FEC are just two fellows with keen eyes. Nothing ground breaking in these pictures whatsoever. People have dressed like this for 100 years. Stop with the prattling on, peanut gallery. Go out and buy some chinos and an oxford shirt. There. Done.

    • Tara

      Fred, the gentleman and business man, is just as dashing and impressive as the man we see as a style blogger and fashion photographer. Great feature.

    • JB

      the thing about “rules” is that they become useless when an individual already looks good. F.E looks killer in all these looks, so why would he worry about some rule that’s designed to
      make you look good?

      it’d be like criticizing an awesome photograph for not composing with thirds
      or something equally dumb.

      killed it F.E, your blog led me to Dan’s a while back – always check both regularly.

    • Joey Dee

      Wow. Every outfit pops! Noone does it better than Style Blogger and FEC.

    • Zulhilmi Rahman

      One of the best influence fashion blogger combined with the one of the best prep master.

    • JAileen

      The tucked in sweater might look good on ataller, thinner person, but makes Mr. Castleberry look very pudgy. Whether it is preppy or not, is not for me to say, but it is not a good look for him.

      • F.E. Castleberry

        I think I’m going to go for a jog now.

        • Khalid

          I don’t think the tucked-in sweater looks bad on Fred, and these ensembles are generally very strong and well-done, but a bit of exercise is a good thing regardless. :-). May I ask what your measurements are? It really helps in figuring out whether a particular look or item would work for the viewer.

    • Michael

      I was sporting the look of the first photo(jacket and down vest) over the weekend but wore a plaid flannel button down, slim brown corduroy pants (rolled up) and Timberland Abington boots. Your blog and Unabashedly Prep are two style blogs I return to on a regular basis.

    • Adam

      Snow and no socks? #seemslegit

    • alan

      This guy knows how to dress. Very good post.
      Love this site.

    • Enoch Castleberry

      The last look is awesome!

    • Carl

      FEC is the man. ’nuff said.

    • JD

      Very very nice socks. Where can I get some? (first pic)

      • F.E. Castleberry

        You can pick up socks like these from Rugby.

    • Chris

      The painted chinos are really cool, not sure I like the tie paired with them though. Neat to see FE’s unique style combined with the styleblogger photography.

    • Tito

      All I have to say is BOOOOOOOOOOOOOOOOOM!
      Fred I love you for this one men!

    • Bruce Shen

      Hey Fred, big fan of your blog, just wondering how you keep your socks looking so straight and crisp. Whenever I wear socks, they end up falling. Do you go with sock garters??


      • F.E. Castleberry

        I rarely wear socks, so when I do they have all their elasticity in them. It sounds like you may need to replace your socks more frequently.

        • Bruce Shen

          Thanks for the reply. Some of the socks are pretty recent. Some are brand new. I do have enormous calves though and probably a minute into walking around I feel the socks slipping down. Sometimes even over the calves socks (cause they only go slightly over) have the same problem.


          • NY

            I have the same problem, Bruce. You’ve got to go full-on knee socks. Calvin Klein makes some good ones, Gold-Toe makes some very affordable ones.

    • andrew

      size of the club monaco trench? i have the same one in a S and its pretty hard to wear over a suit. thanks!

      • F.E. Castleberry

        My trench is a medium.

    • JR

      Monogramming. Oh dear.

    • DBCC

      Looks 3 and 4 are straight killing it, Fred. I especially love look 4. I rarely see you suited up, yet you pull it off so well.

    • alin


      • alin

        Cool article btw

    • Levi

      I really dig this guy’s style and read his blog daily, but I’m not feeling some of the looks in this post. The painted pants are alright. Not many could get away with them, but he does. EXCEPT when paired with, not only a tweed, but a denim jacket as well. Very “try hard” and is about as contrived as you can get.

      You can get away with the down vest over the suit, because it’s the only “out there” thing in the outfit. Like I said, love unabashedly prep, but I feel like he had too many cool things to show us in too few looks. Just my opinion! I liked the post nonetheless.

      The rule on tucking in the sweater is: DON’T. No matter how cool your belt is.

    • Kyle Norville

      Once I seen the post I clicked on it before the page finished loading.

      I love the blend with the custom chinos. Most definitely unique, and controversial. But F.E sure does look comfortable in em. That’s how style should be. comfortable.

      Another one of my favorite posts this month. Keep it up TSB!!!

    • HarrisonK

      Nice post.

      I really like the casual outfit, it’s just about what I wear everyday. What is the rule on tucking in the sweater?

      • F.E. Castleberry

        Harrison, my sweaters are typically partially tucked in…I like showing I have a waist ;)

    • Joe Schmoe

      I remember when ol’ Freddy was a wedding photographer. Guess that didn’t pan out, eh?

      • F.E. Castleberry

        I remember my days as a wedding photographer too. It panned out just fine.

    • cam

      hey dan, hope all is well. fred knows i’m a fan. keep it up!

    • douglas

      Is it just me, or did J. Crew sell the same pants with the paint on them a year ago? Maybe I’m mistaken

      • F.E. Castleberry

        I honestly have no clue.

        • John

          They did. I work for them. Inspired or copied? Hmmm….

    • OTC

      Fred – a great collection of looks. Clever, inspired and fun, but not contrived.

      What really caught my attention was the vintage Omega Seamaster. My dad has the exact same watch and also wears it on a dark brown alligator strap. He is one of the classiest guys I know, particularly because he knows of no other way to dress – it’s simply his style. The watch is vintage because he’s had it for so long and he dresses old school, because that’s what he grew up wearing and he wears things until they fall apart.

      You have done a wonderful job chronicling the reinterpretation of East Coast prep and injecting a fresh perspective into a timeless style.

      Thanks Fred.

      • F.E. Castleberry

        OTC, thanks for sharing that story about your dad and his Seamaster. Before I acquired it, my watch belonged to a great American Indian chief…it was on a southwester navajo type band before it came to rest on my alligator strap. It’s seen a few things I’m sure.

    • Old English

      The puffer jacket with the sport coat is a bit too far. It looks like a costume. Diggin’ all the rest. Great work, as always, SB.


    • Sallie Lin

      Love all from Egan’s style

      • F.E. Castleberry

        Thank you Aunt Sallie. You are incredibly kind and sweet for checking this out.

    • Nikolaj

      The best dressed man right now!

    • windsorite

      New fav post. Fred’s style is unreal and most importantly, hes the nicest blogger around.

    • Caroline @ Back Down South


    • Emanuel Iuhas

      Awesome man!
      Thank you!
      My favourite?The last one!
      Regards from Romania!

    • TO

      This guy’s style is immaculate. Been a fan of his work for a while now:) Classic with a twist is one of the best looks I’ve seen in sometime- the black watch plaid bag and orange belt are quite unexpected indeed!

      Keep killin’ it FEC! Great feature SB!

    • Ambyr

      This “find your casual” look is fantastic. It’s still polished off and preppy. He has great style.


    • Gary-A

      Blue trucker jacket and blue chinos. Absolute perfection.

      Good to see FEC and SB together! Where was this shot? Some gorgeous streets and facades in these pictures too.

    • Big Jon

      I read F.E.’s blog all the time. He’s awesome!